Location: NYC NoHo Office (5 days a week) About This Opportunity We're building something unusual at Automattic : an AI-native culture at a 1,500-person company that powers 40% of the web. Not just adopting AI tools, but fundamentally transforming how we work and ship products at scale. You’ll own the operational infrastructure that makes this possible. The messy, critical work between “we should use AI” and “we’re actually using AI effectively across 1,500 people”: privacy reviews, tool evaluations, policy development, vendor coordination, adoption tracking, and being the person who can answer “should we use this tool?” and “how should we approach this?” This isn’t traditional program management. You’re building the governance frameworks and operational practices that help a distributed, highly technical organization move faster with AI while managing risk appropriately. You’ll work in-person with our Head of AI and NYC AI team while supporting AI adoption globally....

Location: NYC NoHo Office (5 days a week) About This Opportunity Build the AI tools that Automattic uses internally. Maintain and extend LibreChat, our self-hosted AI interface. Create lightweight integrations and automations that make teams more productive. Help 1,500 people work better with AI. This isn’t about building consumer products or shipping to millions of users. It’s about building tools for the people sitting next to you, getting immediate feedback, and iterating based on what actually helps. If you’ve ever wished you could control your own AI tools, customize them exactly how you want, and not be at the mercy of third-party vendors, this is that opportunity. You’ll work in-person with our NYC AI team while your tools serve Automattic’s distributed organization globally. Why This Role Matters Most companies are locked into third-party AI tools: ChatGPT, Claude, whatever comes next. They’re stuck with whatever features the vendor ships, whatever...

Location: New York City (In-person) About This Opportunity We’re assembling an exceptional team of AI engineers in NYC. The kind of people who’ve shipped breakthrough AI products that millions actually use. This isn’t about office amenities or typical startup perks (although we have those too!). It’s about working alongside some of the most talented engineers and product minds in AI, solving fascinating problems at scale. You’ll collaborate in-person with a carefully selected group designed for breakthrough thinking, backed by the resources and reach of Automattic’s ecosystem, spanning WordPress.com , WooCommerce , Tumblr , and more. Think of it as an elite AI lab with the distribution and impact of Automattic’s broad and deep ecosystem. What You’ll Do Ship user-facing AI features across Automattic’s product ecosystem; from content creation tools to e-commerce recommendations to messaging experiences. Build and iterate rapidly on AI-powered products...

At  WordPress VIP (part of Automattic ), we power the most influential properties on the web, from the White House to Meta and Salesforce. We are looking for a Forward Deployed Engineer (FDE) to join our mission in redefining how the world’s largest enterprises scale. This isn't your typical engineering role; it’s an advanced, consultative position where you operate as a hands-on architect and a growth catalyst. As an FDE, you are the front line of trust, embedded with our most strategic customers to solve high-stakes technical challenges in real-time. By combining engineering excellence with deep customer proximity, you won’t just solve problems for customers, you’ll solve them with them, driving business expansion across the world’s most scaled environments. If you thrive in high-impact, ambiguous environments and want to help define the future of open-source technology at the enterprise level, we want to talk to you. About the Team The Customer Engineering and...